1. Field of the Invention
This invention relates to a method for producing (R,Z)-5-tetradecen-4-olide. The present substance is a sex pheromone of a Japanese beetle (scientific name: Popillia japonica). This compound is useful for the extermination of the Japanese beetle through a pheromone trap.
2. Description of the Related Art
Japanese beetles are insect pests which live on fruit trees or, for instance grapes, lawn, etc. In recent years, a damaged lawn by Japanese beetles have become a problem especially on a golf course. Moreover, since a large amount of pesticides are used for extermination of Japanese beetles, pesticide pollution has caused a public discussion in the area near to a golf course.
Pheromone traps are able to exterminate a large amount of insect pests by utilizing a small amount of pheromone, and is practically applied for some insects. A pheromone trap against the Japanese beetle is therefore considered to be a useful means in order to solve said problem.
A method described in Agric. Biol. Chem., 51, 635-640 (1987) is known as a method for synthesizing a pheromone of Japanese beetle, i.e., (R,Z)-5-tetradecen-4-olide. This method is performed by synthesizing from arabinose an optically-active intermediate, (4R, 5S, 6R)-5,6-dihydroxytetradecan-4-olide, and then by eliminating diol from said intermediate according to the following steps: ##STR2##
However, this conventional method includes a step for utilizing chromic acid, a harmful reagent, as an oxidizing agent in order to synthesize the optically-active intermediate, (4R,5S,6R)-5,6-dihydroxytetradecan-4-olide. This method thus suffers from problems on practical use in that it lowers safety in synthesis manipulation and it causes environmental pollution through industrial waste.